Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes

Naoya Ohmura, Asami Nakamura, Akiyuki Hamasaki, Makoto Tokunaga

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed.

Original languageEnglish
Pages (from-to)5042-5045
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number30
DOIs
Publication statusPublished - Oct 2008

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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